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Method for preparing cinnamic alcohol by hydrogen transfer reaction of benzalacet aldehyde

A technology of cinnamaldehyde and cinnamyl alcohol is applied in chemical instruments and methods, preparation of hydroxyl compounds, preparation of organic compounds, etc., can solve problems such as unreported, and achieve the effects of low cost, simple preparation conditions, and improved conversion rate

Inactive Publication Date: 2009-01-21
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation of metal oxide catalysts as supported catalysts can further improve its catalytic performance, but the application of supported ZrOx catalysts with simple preparation conditions using inorganic zirconium salts as active component precursors and water as a solvent has not yet been used in this reaction. See the report; Simultaneously, how to suppress the poisoning effect of cinnamic acid to the catalyst in the reaction process is also not seen in the report

Method used

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  • Method for preparing cinnamic alcohol by hydrogen transfer reaction of benzalacet aldehyde
  • Method for preparing cinnamic alcohol by hydrogen transfer reaction of benzalacet aldehyde
  • Method for preparing cinnamic alcohol by hydrogen transfer reaction of benzalacet aldehyde

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1. is catalyst with ZrOx / Si-MCM-41, ZrO loading is different

[0025] The preparation process of ZrOx / Si-MCM-41 catalyst is as follows: Weigh 0.112~2.8g Zr(NO 3 ) 4 ·5H 2 O, dissolved in 200ml of deionized water, added 3g of all-silicon MCM-41 mesoporous molecular sieve carrier, stirred for 24h, distilled under reduced pressure at 40-60°C for 4-6h, centrifuged, and dried at 100°C for 10h to obtain the Zr loading capacity 1% to 25% ZrOx / Si-MCM-41 catalyst.

[0026] Take 1 g of catalysts with different loads and treat them in air at 573K for 5 hours. The hydrogen transfer reaction of cinnamaldehyde was carried out in a 25ml round bottom flask under normal pressure and a reaction temperature of 76°C. Add 3mmol cinnamaldehyde, 60mmol isopropanol, 0.3g catalyst and a certain amount of triethylamine (the molar ratio of triethylamine to Zr is 1.5:1) into the flask, stir magnetically, and reflux water at 20°C to condense. Both isopropanol and cinnamaldehyde were...

Embodiment 2

[0029] Embodiment 2. is catalyst with 5%ZrOx / Si-MCM-41, and reaction time is different

[0030] The preparation process of the 5%ZrOx / Si-MCM-41 catalyst and the pretreatment process before use are the same as those described in Example 1, and the reaction and analysis conditions are also basically the same, the difference being that regular sampling and analysis during the reaction process. Table 2 shows the conversion of cinnamaldehyde over the 5% ZrOx / Si-MCM-41 catalyst with the reaction time.

[0031] The conversion situation of cinnamaldehyde on 5%ZrOx / Si-MCM-41 catalyst under the different reaction times of table 2

[0032]

Embodiment 3

[0033] Embodiment 3. is catalyst with 5%ZrOx / Si-MCM-41, and raw material charging ratio is different

[0034] The preparation process of 5%ZrOx / Si-MCM-41 catalyst and the pretreatment process before use are identical with that described in embodiment 1, and reaction and analysis condition are also substantially identical, and difference is the feed ratio of cinnamaldehyde and Virahol different. Table 3 shows the conversion of cinnamaldehyde on 5% ZrOx / Si-MCM-41 catalyst with different feed ratios of cinnamaldehyde and isopropanol.

[0035] The conversion situation of cinnamaldehyde on 5%ZrOx / Si-MCM-41 catalyst when table 3 different cinnamaldehyde and isopropanol feed ratio

[0036]

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Abstract

The invention discloses a method for preparing cinnamic alcohol through hydrogen transfer reaction of cinnamaldehyde. The method comprises the following steps that under the conditions of normal pressure and 70 to 90 DEG C, cinnamaldehyde is reduced to obtain cinnamic alcohol through taking supported ZrOx as a catalyst and alcohol as a reducing agent in the presence of catalyst acid poisoning inhibitor organic base. The method adopts the supported ZrOx as the catalyst which is prepared through taking inorganic zircon salt as active ingredient precursor and water as solvent; therefore, the catalyst has the advantages of simple preparation conditions, relatively low cost and excellent catalytic performance; moreover, the organic base is added as the catalyst acid poisoning inhibitor for preparing cinnamic alcohol through hydrogen transfer reaction of cinnamaldehyde, thereby greatly increasing the conversion rate of the cinnamaldehyde. Therefore, the method can generate cinnamic alcohol through the reduction of the cinnamaldehyde in high conversion rate and high selectivity, and is suitable for carrying out large-scale industrial production.

Description

(1) Technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a method for preparing cinnamyl alcohol through hydrogen transfer reaction of cinnamaldehyde under the catalysis of supported zirconia. (2) Background technology [0002] Cinnamyl alcohol (COL) is a fine organic product with high added value, which can be used as an important raw material and intermediate in the production of spices, medicines and other fine chemical products, and is also widely used in organic synthesis. The production of cinnamyl alcohol is usually prepared by heat-treating natural sage oil, Peruvian gum and cinnamon oil with caustic alkali, which has high production cost, low yield and serious environmental pollution. The selective reduction of cinnamaldehyde (CAL) to prepare cinnamyl alcohol is not only cheap, but also conducive to large-scale production. There are conjugated C=C, C=O and benzene ring structures in the cinnamaldehyd...

Claims

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Application Information

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IPC IPC(8): C07C33/32C07C29/141B01J29/70
Inventor 张波金滨李秀娟葛忠华
Owner ZHEJIANG UNIV OF TECH
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